# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 30 00:50:16 2022
#   Inital geometry file: a 99 line input string
#   Ligand name: (4R)-3-methyl-5-[(4R)-4-methyl-3,4-dihydroisoquinolin-2(1H)-yl]thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H]1CN(Cc2ccccc12)c3nc4ccsc4c5nnc(C)n35
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 8IE  8IE  "(4R)-3-methyl-5-[(4R)-4-methyl-3,4-dihydroisoquinolin-2(1H)-yl]thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine"
  ligand  41  24  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_8IE
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 8IE  C10  C  CR16  0  -0.260  23.1971  57.8939  23.2292
 8IE  C15  C  CR56  0  -0.317  16.4283  57.1177  28.3730
 8IE  C17  C  CR15  0  -0.458  14.0006  57.2272  28.1188
 8IE  C22  C  CR5   0   0.404  19.9059  57.5440  28.3803
 8IE  C01  C  CH3   0  -0.669  19.6654  61.5973  23.3814
 8IE  C02  C  CR16  0  -0.316  20.0421  60.5787  24.4543
 8IE  C03  C  C     0  -0.284  18.7886  59.8232  24.8824
 8IE  C05  C  C     0  -0.368  19.8593  57.6859  24.9858
 8IE  C06  C  CR66  0   0.032  21.0560  58.2632  24.2854
 8IE  C07  C  CR66  0   0.126  21.1407  59.6305  24.0186
 8IE  C08  C  CR16  0  -0.307  22.2804  60.1091  23.3709
 8IE  C09  C  CR16  0  -0.251  23.2984  59.2559  22.9759
 8IE  C11  C  CR16  0  -0.287  22.0793  57.4072  23.8855
 8IE  C12  C  CR6   0   0.671  18.2045  58.2523  26.6129
 8IE  C14  C  CR56  0   0.285  16.0477  57.8303  27.2521
 8IE  C18  C  CR15  0  -0.188  14.6302  57.8882  27.1151
 8IE  C19  C  CR56  0   0.491  17.8051  57.0353  28.6698
 8IE  N04  N  NR6   0  -0.518  19.1671  58.7208  25.7506
 8IE  N13  N  N     0  -0.460  16.9481  58.3604  26.3727
 8IE  N20  N  N     0  -0.333  18.4663  56.5637  29.6861
 8IE  N21  N  N     0  -0.312  19.7668  56.8901  29.4946
 8IE  N24  N  N     0  -0.608  18.6655  57.6481  27.7793
 8IE  S16  S  S2    0   0.263  15.0886  56.5222  29.2542
 8IE  H1   H  HCR6  0   0.253  23.9874  57.2188  22.9278
 8IE  H2   H  HCR5  0   0.309  12.9377  57.1063  28.2614
 8IE  H3   H  HCH3  0   0.237  18.8499  62.2306  23.7340
 8IE  H4   H  HCH3  0   0.242  20.4948  62.2547  23.1261
 8IE  H5   H  HCH3  0   0.228  19.3347  61.0997  22.4685
 8IE  H6   H  HCR6  0   0.256  20.4078  61.1254  25.3312
 8IE  H7   H  H     0   0.266  18.1253  60.4992  25.4200
 8IE  H8   H  H     0   0.228  18.2422  59.4626  23.9999
 8IE  H9   H  H     0   0.271  19.1690  57.2504  24.2482
 8IE  H10  H  H     0   0.275  20.1658  56.8651  25.6345
 8IE  H11  H  HCR6  0   0.249  22.3793  61.1687  23.1705
 8IE  H12  H  HCR6  0   0.252  24.1710  59.6542  22.4743
 8IE  H13  H  HCR6  0   0.250  21.9991  56.3476  24.1006
 8IE  H14  H  HCR5  0   0.280  14.1221  58.3920  26.3059
 8IE  H15  H  HCH3  0   0.274  21.9063  58.0360  28.7297
 8IE  H16  H  HCH3  0   0.266  21.6011  57.6099  27.0523
 8IE  H17  H  HCH3  0   0.269  21.0832  59.1784  27.6599
 8IE  C23  C  CH3   0  -0.739  21.1886  58.1267  27.9176

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 8IE  C10  C09  aromatic  1.389  0.020  1.389
 8IE  C10  C11  aromatic  1.385  0.020  1.385
 8IE  C09  C08  aromatic  1.386  0.020  1.386
 8IE  C11  C06  aromatic  1.393  0.020  1.393
 8IE  C08  C07  aromatic  1.395  0.020  1.395
 8IE  C06  C07  aromatic  1.396  0.020  1.396
 8IE  C06  C05  single    1.502  0.020  1.502
 8IE  C07  C02  single    1.515  0.020  1.515
 8IE  C05  N04  single    1.461  0.020  1.461
 8IE  C01  C02  single    1.527  0.020  1.527
 8IE  C02  C03  single    1.525  0.020  1.525
 8IE  C03  N04  single    1.453  0.020  1.453
 8IE  N04  C12  single    1.375  0.020  1.375
 8IE  N13  C12  aromatic  1.284  0.020  1.284
 8IE  N13  C14  aromatic  1.366  0.020  1.366
 8IE  C12  N24  aromatic  1.392  0.020  1.392
 8IE  C18  C14  aromatic  1.425  0.020  1.425
 8IE  C18  C17  aromatic  1.357  0.020  1.357
 8IE  C14  C15  aromatic  1.382  0.020  1.382
 8IE  N24  C22  aromatic  1.382  0.020  1.382
 8IE  N24  C19  aromatic  1.382  0.020  1.382
 8IE  C23  C22  single    1.483  0.020  1.483
 8IE  C17  S16  aromatic  1.723  0.020  1.723
 8IE  C15  C19  aromatic  1.411  0.020  1.411
 8IE  C15  S16  aromatic  1.711  0.020  1.711
 8IE  C22  N21  aromatic  1.299  0.020  1.299
 8IE  C19  N20  aromatic  1.301  0.020  1.301
 8IE  N21  N20  aromatic  1.354  0.020  1.354
 8IE  C10  H1   single    0.930  0.020  1.080
 8IE  C17  H2   single    0.930  0.020  1.080
 8IE  C01  H3   single    0.970  0.020  1.090
 8IE  C01  H4   single    0.970  0.020  1.090
 8IE  C01  H5   single    0.970  0.020  1.090
 8IE  C02  H6   single    0.970  0.020  1.090
 8IE  C03  H7   single    0.970  0.020  1.090
 8IE  C03  H8   single    0.970  0.020  1.090
 8IE  C05  H9   single    0.970  0.020  1.090
 8IE  C05  H10  single    0.970  0.020  1.090
 8IE  C08  H11  single    0.930  0.020  1.080
 8IE  C09  H12  single    0.930  0.020  1.080
 8IE  C11  H13  single    0.930  0.020  1.080
 8IE  C18  H14  single    0.930  0.020  1.080
 8IE  C23  H15  single    0.970  0.020  1.090
 8IE  C23  H16  single    0.970  0.020  1.090
 8IE  C23  H17  single    0.970  0.020  1.090

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 8IE  H1   C10  C11  120.15  3.000
 8IE  H1   C10  C09  120.50  3.000
 8IE  C11  C10  C09  119.34  3.000
 8IE  S16  C15  C19  129.46  3.000
 8IE  S16  C15  C14  112.44  3.000
 8IE  C19  C15  C14  118.01  3.000
 8IE  H2   C17  S16  119.27  3.000
 8IE  H2   C17  C18  127.55  3.000
 8IE  S16  C17  C18  113.18  3.000
 8IE  N24  C22  N21  108.34  3.000
 8IE  N21  C22  C23  123.91  3.000
 8IE  N24  C22  C23  127.66  3.000
 8IE  H5   C01  H4   108.07  3.000
 8IE  H5   C01  H3   107.98  3.000
 8IE  H4   C01  H3   107.14  3.000
 8IE  H5   C01  C02  111.01  3.000
 8IE  H4   C01  C02  112.31  3.000
 8IE  H3   C01  C02  110.16  3.000
 8IE  H6   C02  C07  107.48  3.000
 8IE  H6   C02  C03  107.26  3.000
 8IE  C07  C02  C03  111.51  3.000
 8IE  H6   C02  C01  108.17  3.000
 8IE  C03  C02  C01  108.96  3.000
 8IE  C07  C02  C01  113.23  3.000
 8IE  H8   C03  H7   107.30  3.000
 8IE  H8   C03  N04  111.12  3.000
 8IE  H7   C03  N04  109.54  3.000
 8IE  H8   C03  C02  110.24  3.000
 8IE  H7   C03  C02  109.37  3.000
 8IE  N04  C03  C02  109.23  3.000
 8IE  H10  C05  H9   106.10  3.000
 8IE  H10  C05  N04  110.79  3.000
 8IE  H9   C05  N04  109.51  3.000
 8IE  H10  C05  C06  110.05  3.000
 8IE  H9   C05  C06  109.85  3.000
 8IE  N04  C05  C06  110.45  3.000
 8IE  C11  C06  C07  120.17  3.000
 8IE  C07  C06  C05  120.93  3.000
 8IE  C11  C06  C05  118.89  3.000
 8IE  C08  C07  C06  118.31  3.000
 8IE  C06  C07  C02  120.94  3.000
 8IE  C08  C07  C02  120.73  3.000
 8IE  H11  C08  C09  118.86  3.000
 8IE  H11  C08  C07  119.74  3.000
 8IE  C09  C08  C07  121.40  3.000
 8IE  H12  C09  C08  119.85  3.000
 8IE  H12  C09  C10  120.28  3.000
 8IE  C08  C09  C10  119.88  3.000
 8IE  H13  C11  C06  119.29  3.000
 8IE  H13  C11  C10  119.82  3.000
 8IE  C06  C11  C10  120.88  3.000
 8IE  N24  C12  N13  121.16  3.000
 8IE  N24  C12  N04  116.21  3.000
 8IE  N13  C12  N04  122.64  3.000
 8IE  N13  C14  C18  125.31  3.000
 8IE  C18  C14  C15  111.89  3.000
 8IE  N13  C14  C15  122.75  3.000
 8IE  H14  C18  C14  123.97  3.000
 8IE  H14  C18  C17  124.27  3.000
 8IE  C14  C18  C17  111.76  3.000
 8IE  N24  C19  N20  110.36  3.000
 8IE  N20  C19  C15  132.96  3.000
 8IE  N24  C19  C15  116.50  3.000
 8IE  C12  N04  C05  114.75  3.000
 8IE  C12  N04  C03  116.80  3.000
 8IE  C05  N04  C03  110.36  3.000
 8IE  C14  N13  C12  119.48  3.000
 8IE  N21  N20  C19  106.86  3.000
 8IE  N20  N21  C22  110.20  3.000
 8IE  C19  N24  C12  121.76  3.000
 8IE  C19  N24  C22  104.19  3.000
 8IE  C12  N24  C22  133.96  3.000
 8IE  C17  S16  C15   90.72  3.000
 8IE  H17  C23  H16  107.89  3.000
 8IE  H17  C23  H15  108.75  3.000
 8IE  H16  C23  H15  107.68  3.000
 8IE  H17  C23  C22  111.72  3.000
 8IE  H16  C23  C22  112.89  3.000
 8IE  H15  C23  C22  107.76  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 8IE  CONST_01  C07  C08  C09  C10     0.00   0.0  0
 8IE  CONST_02  C07  C06  C11  C10     0.00   0.0  0
 8IE  CONST_03  C12  N13  C14  C15     0.00   0.0  0
 8IE  CONST_04  C17  C18  C14  C15     0.00   0.0  0
 8IE  CONST_05  C12  N24  C19  C15     0.00   0.0  0
 8IE  CONST_06  C22  N24  C19  C15   180.00   0.0  0
 8IE  CONST_07  N21  N20  C19  C15   180.00   0.0  0
 8IE  CONST_08  C18  C17  S16  C15     0.00   0.0  0
 8IE  CONST_09  N13  C14  C18  C17   180.00   0.0  0
 8IE  CONST_10  C14  C15  S16  C17     0.00   0.0  0
 8IE  CONST_11  C19  C15  S16  C17   180.00   0.0  0
 8IE  CONST_12  N13  C12  N24  C22   180.00   0.0  0
 8IE  CONST_13  N20  C19  N24  C22     0.00   0.0  0
 8IE  CONST_14  C19  N20  N21  C22     0.00   0.0  0
 8IE  CONST_15  C09  C10  C11  C06     0.00   0.0  0
 8IE  CONST_16  C09  C08  C07  C06     0.00   0.0  0
 8IE  CONST_17  C12  N04  C05  C06   180.00   0.0  0
 8IE  CONST_18  C11  C10  C09  C08     0.00   0.0  0
 8IE  CONST_19  C11  C06  C07  C08     0.00   0.0  0
 8IE  CONST_20  C18  C14  N13  C12   180.00   0.0  0
 8IE  CONST_21  N21  C22  N24  C12   180.00   0.0  0
 8IE  CONST_22  N20  C19  N24  C12   180.00   0.0  0
 8IE  CONST_23  N24  C12  N13  C14     0.00   0.0  0
 8IE  CONST_24  S16  C17  C18  C14     0.00   0.0  0
 8IE  CONST_25  N24  C19  C15  C14     0.00   0.0  0
 8IE  CONST_26  N20  C19  C15  C14   180.00   0.0  0
 8IE  CONST_27  C19  C15  C14  C18   180.00   0.0  0
 8IE  CONST_28  S16  C15  C14  C18     0.00   0.0  0
 8IE  CONST_29  N13  C12  N24  C19     0.00   0.0  0
 8IE  CONST_30  N21  C22  N24  C19     0.00   0.0  0
 8IE  CONST_31  N13  C14  C15  C19     0.00   0.0  0
 8IE  CONST_32  S16  C15  C14  N13   180.00   0.0  0
 8IE  CONST_33  S16  C15  C19  N20     0.00   0.0  0
 8IE  CONST_34  N24  C22  N21  N20     0.00   0.0  0
 8IE  CONST_35  N24  C19  N20  N21     0.00   0.0  0
 8IE  CONST_36  S16  C15  C19  N24   180.00   0.0  0
 8IE  CONST_37  N04  C12  N24  C22     0.00   0.0  0
 8IE  CONST_38  N04  C12  N13  C14   180.00   0.0  0
 8IE  CONST_39  N04  C12  N24  C19   180.00   0.0  0
 8IE  CONST_40  C23  C22  N24  C12     0.00   0.0  0
 8IE  CONST_41  C23  C22  N24  C19   180.00   0.0  0
 8IE  CONST_42  N20  N21  C22  C23   180.00   0.0  0
 8IE  CONST_43  H11  C08  C09  C10   180.00   0.0  0
 8IE  CONST_44  H14  C18  C14  C15   180.00   0.0  0
 8IE  CONST_45  H2   C17  S16  C15   180.00   0.0  0
 8IE  CONST_46  H11  C08  C07  C02     0.00   0.0  0
 8IE  CONST_47  H13  C11  C06  C05     0.00   0.0  0
 8IE  CONST_48  H1   C10  C11  C06   180.00   0.0  0
 8IE  CONST_49  H11  C08  C07  C06   180.00   0.0  0
 8IE  CONST_50  H12  C09  C08  C07   180.00   0.0  0
 8IE  CONST_51  H13  C11  C06  C07   180.00   0.0  0
 8IE  CONST_52  H1   C10  C09  C08   180.00   0.0  0
 8IE  CONST_53  H13  C11  C10  C09   180.00   0.0  0
 8IE  CONST_54  H12  C09  C10  C11   180.00   0.0  0
 8IE  CONST_55  H2   C17  C18  C14   180.00   0.0  0
 8IE  CONST_56  H14  C18  C14  N13     0.00   0.0  0
 8IE  CONST_57  H14  C18  C17  S16   180.00   0.0  0
 8IE  Var_01    C05  N04  C03  C02   -70.19  30.0  1
 8IE  Var_02    C12  N04  C03  C02   156.36  30.0  1
 8IE  Var_03    C06  C05  N04  C03    56.56  30.0  1
 8IE  Var_04    N13  C12  N04  C03    26.33  30.0  2
 8IE  Var_05    N24  C12  N04  C03  -153.52  30.0  2
 8IE  Var_06    N13  C12  N04  C05  -105.13  30.0  2
 8IE  Var_07    N24  C12  N04  C05    75.02  30.0  2
 8IE  Var_08    N04  C05  C06  C07   -22.11  30.0  1
 8IE  Var_09    N04  C05  C06  C11   158.80  30.0  1
 8IE  Var_10    H9   C05  N04  C03   -64.54  30.0  1
 8IE  Var_11    H10  C05  N04  C03   178.76  30.0  1
 8IE  Var_12    H7   C03  N04  C05   170.04  30.0  1
 8IE  Var_13    H8   C03  N04  C05    51.65  30.0  1
 8IE  Var_14    H9   C05  C06  C07    98.79  30.0  1
 8IE  Var_15    H10  C05  C06  C07  -144.75  30.0  1
 8IE  Var_16    H9   C05  C06  C11   -80.30  30.0  1
 8IE  Var_17    H10  C05  C06  C11    36.16  30.0  1
 8IE  Var_18    H9   C05  N04  C12    69.94  30.0  1
 8IE  Var_19    H10  C05  N04  C12   -46.76  30.0  1
 8IE  Var_20    H7   C03  N04  C12    36.59  30.0  1
 8IE  Var_21    H8   C03  N04  C12   -81.80  30.0  1
 8IE  Var_22    H15  C23  C22  N21    -8.42  30.0  2
 8IE  Var_23    H16  C23  C22  N21   110.37  30.0  2
 8IE  Var_24    H17  C23  C22  N21  -127.82  30.0  2
 8IE  Var_25    H15  C23  C22  N24   167.75  30.0  2
 8IE  Var_26    H16  C23  C22  N24   -73.47  30.0  2
 8IE  Var_27    H17  C23  C22  N24    48.35  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 8IE  chir_01  C02  C07  C01  C03  negativ

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 8IE  plan-1  C10  0.020
 8IE  plan-1  C02  0.020
 8IE  plan-1  C05  0.020
 8IE  plan-1  C06  0.020
 8IE  plan-1  C07  0.020
 8IE  plan-1  C08  0.020
 8IE  plan-1  C09  0.020
 8IE  plan-1  C11  0.020
 8IE  plan-1  H1   0.020
 8IE  plan-1  H11  0.020
 8IE  plan-1  H12  0.020
 8IE  plan-1  H13  0.020
 8IE  plan-2  C15  0.020
 8IE  plan-2  C17  0.020
 8IE  plan-2  C14  0.020
 8IE  plan-2  C18  0.020
 8IE  plan-2  C19  0.020
 8IE  plan-2  N13  0.020
 8IE  plan-2  S16  0.020
 8IE  plan-2  H2   0.020
 8IE  plan-2  H14  0.020
 8IE  plan-3  C15  0.020
 8IE  plan-3  C22  0.020
 8IE  plan-3  C12  0.020
 8IE  plan-3  C19  0.020
 8IE  plan-3  N20  0.020
 8IE  plan-3  N21  0.020
 8IE  plan-3  N24  0.020
 8IE  plan-3  C23  0.020

